Vacation rentals in Chesterfield

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Chesterfield

  • Total vacation rentals

    Explore 130 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at G$6,261 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,120 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Chesterfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

  • 4.8 Average rating

    Chesterfield stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cottage in Chesterfield
4.93 out of 5 average rating, 339 reviews

Chatsworth Cottage

Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.

LocationValueWalkability

Top guest favorite
A well-maintained pathway leads to a beautifully designed cottage surrounded by lush greenery. The property features manicured hedges and trees, with a clear blue sky overhead, creating a welcoming entrance to the private garden area.
Guesthouse in Derbyshire
4.99 out of 5 average rating, 196 reviews

Springwood Cottage Private and Unique

Springwood Cottage is ideally situated in a beautiful location on the edge of Derbyshire is completely self contained with its own entrance and private garden area with parking outside. The Cottage is completely newly built in 2020 and designed to the highest standard. Well behaved Dogs welcome, we are happy to accommodate 2 dogs, please request if you have more than 2. A deluxe super kingsized bed (6 x6 foot) with the most up to date memory foam mattress and a comfortable sofa bed in the lounge

FamilyValueTV

Top guest favorite
A cosy living room features comfortable seating on two plush sofas, arranged around a central ottoman. A stone fireplace with a woodburner creates a focal point. Exposed beams highlight the ceiling, while the space is adorned with floral cushions and a decorative area rug.
Cottage in Baslow
4.94 out of 5 average rating, 343 reviews

Characterful 2 bed cottage in excellent location

A charming cottage overlooking a babbling, nature-rich brook. Full of character, this peaceful cottage boasts a cosy living room complete with woodburner, underfloor heating and exposed beams, a fabulous kitchen and a stylish bathroom. The cottage is in a superb location with top-class restaurants, the magnificent Chatsworth Estate and truly stunning local walks right on the doorstep. Bikes can be stored in the rear yard making this cottage an ideal base for foodies, cyclists and walkers alike.

ValueFamilyComfort

Top guest favorite
The Tower emerges from a lush green landscape, surrounded by tall trees and manicured grass. The building's robust concrete structure is accented by its original window designs, reflecting the natural beauty of the outdoors in a tranquil setting.
Tower in Bolsover
5.0 out of 5 average rating, 246 reviews

The Tower

The Tower is the perfect romantic high-end getaway for couples who want to get away from it all in a secluded location and fancy just something different. The Tower has recently been converted for use as a holiday let which was previously an unused ancillary building adjacent to The Water Works, an old water treatment plant near Bolsover, converted to domestic use in 2002 and featured on the Channel 4 programme Grand Designs. Available for single night stays. Discounts on 3+ nights bookings.

ValueFamilyTV

Top guest favorite
A spacious lawn leads to a charming stone cottage, surrounded by well-maintained greenery. The bright blue sky and scattered clouds enhance the inviting atmosphere, while the driveway provides access to the property and its scenic surroundings.
Cottage in Derbyshire
5.0 out of 5 average rating, 282 reviews

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

*AirBnB Best New Host Finalist 2022* A stunning 2 bedroom (Sleeps 4) luxury cottage, nestled in the Peak District countryside, with superb views over Chatsworth House. Outdoor dining, farm animals, private parking (with electric charging) & tranquil walks - all within a short drive of Bakewell, Matlock & the beautiful Derbyshire Dale villages. Fully equipped with everything you will need for your stay, including: Netflix, Amazon Prime & Disney+ BBQ for outdoor dining. Family & Dog Friendly

LocationFamilyCondition

Guest favorite
A charming two-story cottage is presented with a welcoming façade featuring pale pink and cream walls. A quiet street is visible alongside, with a parking space indicated. Lush trees line the road, enhancing the serene environment of the neighborhood.
Townhouse in Chesterfield
4.87 out of 5 average rating, 115 reviews

Cottage by the Park Chesterfield - Peak district

Our COTTAGE is situated with a PARK on our doorstep and 15 min drive to Baslow in the PEAK DISTRICT . Also within walking distance to Chesterfield town center and Chatsworth road. Only a 15 min walk to bars, restaurants, coffee shops, and local boutique shops on Chatsworth Road. It is a short drive to Chatsworth house, Bakewell, Matlock and many of the delightful areas in the Peak district. Our home is cozy and welcoming! We hope you will choose us for your next visit to the area.

LocationFamilyBreakfast

Top guest favorite
A spacious room features a large bed with gray bedding and decorative pillows. A cozy armchair in a rich maroon color adds warmth next to an elegant glass table. Natural light enters through arched doors leading to a garden, enhancing the peaceful ambiance.
Apartment in Sheffield
4.98 out of 5 average rating, 614 reviews

The Hollies - Luxury self contained apartment

This garden flat with separate access is located in the heart of Sheffield's academic and healthcare hubs. Nestled between Broomhill, Ecclesall road and 2 miles away from the city centre. Close to Botanical Gardens, Endcliffe park and a short walk to a variety of restaurants and pubs. With an en-suite bathroom, well equipped kitchen and small private patio this apartment is perfect for everything Sheffield has to offer! We have 2 friendly dogs and a cat. We also have free overnight parking.

ValueLocationGetting around

Top guest favorite
An inviting living space is featured, showcasing a modern dining table and chairs alongside a vibrant red sideboard. A cozy armchair and a striped lounge chair add comfort, while softly illuminated pendant lights enhance the room's ambiance. Natural light filters through a window adorned with gray curtains.
Home in Chesterfield
4.91 out of 5 average rating, 114 reviews

Bright - 2 Bedroomed House in Derbyshire

Your family will be close to everything when you stay at this centrally located town house within walking distance from Chesterfield's iconic market town. This 2 bedroomed modern home has everything you need and is the perfect base for visiting all the local attractions Derbyshire has to offer. Right on the edge of the Peak District it boasts a 20 minute drive to Chatsworth House and many more. Along with all the wonderful bars, restaurants, gift & coffee shops all within walking distance.

ValueLocationLaundry

Top guest favorite
A spacious studio is seen, featuring a wooden double bed and a breakfast bar with stools. Comfy chairs are positioned near a large television. Soft carpeted flooring complements the pastel-colored walls, and kitchen appliances are visible in the background, providing functional living space.
Apartment in Chesterfield
4.96 out of 5 average rating, 294 reviews

Cosy studio apartment close to Peak District

Cosy,private ,self contained upstairs studio with own entrance , double bed with en suite, dual ring halogen hob ,combination microwave and oven , television with free sat ,free wifi ,integrated fridge freezer ,breakfast bar and stools . Comfy chairs to relax! On the main bus route into Chesterfield and the Peak District ,10 mins to Chatsworth,20 mins to Bakewell and lots of walks in the area. Many bars ,coffee shops and restaurants within walking distance . We look forward to meeting you.

LocationValueGrill

Top guest favorite
A comfortable living area is furnished with a gray sectional sofa and two leather armchairs. A glass coffee table is positioned centrally, and a wooden cabinet stands against the wall, adding storage space. Double doors lead to the outside, allowing natural light to enter.
Home in Chesterfield
4.96 out of 5 average rating, 351 reviews

The Long Hall 2 bed ground floor annexed apartment

Long Hall has been lovingly converted into a 6-person, ground floor, annexed apartment, within a quiet housing estate, a short distance from the Peak District. Two large double bedrooms, with rainfall shower en-suites, and a large open-plan living area dining and kitchen area and a large, shared enclosed patio and garden area Long Hall suits leisure and tourist staycations, as well as trade or professional workers, who wish for a home from home. SKY Sports and Movies included

LocationFamilySleep quality

Top guest favorite
Barn in Holymoorside
4.99 out of 5 average rating, 192 reviews

Charming grade II listed cottage with hot tub

Chander Hill Cottage is a stylish 3-bedroom barn conversion nestled above the village of Holymoorside, on the edge of the Peak District. This cosy cottage is a perfect base for exploring the countryside, with numerous walks from the door and two pubs just a mile away in the village. Relax in our hot tub with stunning views or warm up by the wood burning stove after a winter walk. The enclosed cottage garden has a patio where you can enjoy a BBQ in the summer. Dogs welcome!

ValueFamilyHeating

Superhost
The living area features a comfortable gray sofa, accompanied by decorative cushions. A light wooden bookshelf holds various books, while a dining table adorned with a vase of roses occupies the foreground. The space is filled with natural light from nearby windows.
Condo in Chesterfield
4.83 out of 5 average rating, 145 reviews

The Corner House A-2 Bedroom Town Centre Apartment

A stylish ground-floor apartment in a beautifully converted 1800s home, recently refurbished to a high standard and exclusively used for Airbnb guests. The property features two double bedrooms, a full bathroom plus a separate toilet, and a fully equipped open-plan kitchen/diner with a sofa bed - perfect for relaxing stays. Within walking distance of Chesterfield town centre and train station, with allocated parking for one car.

FamilyValueGetting around

Popular amenities for Chesterfield vacation rentals

When is the best time to visit Chesterfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$22,748 GYDG$22,957 GYDG$24,418 GYDG$25,670 GYDG$25,461 GYDG$26,296 GYDG$22,957 GYDG$24,835 GYDG$21,705 GYDG$23,374 GYDG$22,539 GYDG$22,957 GYD
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°C

Frequently Asked Questions

  • What are the best places to stay in Chesterfield?

    Look for accommodations around the town center, Hasland, or the Brampton area, which have convenient access to shops and local attractions. Neighborhoods near parks may appeal to those seeking a quieter stay.

  • What are the best things to do in Chesterfield with kids?

    Queen’s Park has playgrounds and open spaces, while local museums and swimming pools provide indoor options. Family-friendly events and seasonal activities add variety throughout the year.

  • What are some of the best things to do in Chesterfield?

    Explore outdoor markets, visit the Church of St Mary and All Saints with its iconic spire, and relax in Queen’s Park. The town has museums, cozy cafés, and easy access to countryside trails.

  • How is the weather in Chesterfield?

    Chesterfield experiences cool winters around 35–44°F (2–7°C), and milder summers averaging 54–71°F (12–22°C). Rain is common year-round, so a waterproof jacket is useful most seasons.

  • When is the best time to visit Chesterfield?

    Late spring and summer are often recommended for milder temperatures and longer daylight hours. Autumn brings colorful foliage, while winter is cooler and tends to be wetter.

  • What are the best places to visit in Chesterfield?

    Enjoy the unique Church of St Mary and All Saints, stroll through Queen’s Park, or discover local history at Chesterfield Museum. The outdoor market brings a lively atmosphere on market days.

  • What are some hiking trails in Chesterfield?

    Explore scenic paths in Queen's Park, wander the countryside around the Peak District, or stroll along canal towpaths. These trails provide a blend of nature, parkland, and gentle walking routes.

  • What are some family activities we can do in Chesterfield?

    Explore the play areas in Queen’s Park, visit local museums, or enjoy leisure centers with swimming and sports facilities. Family walks and outdoor events are frequently suggested on weekends.

  • What are some of the best day trip ideas from Chesterfield?

    Visit the countryside around the Peak District, explore historic stately homes, or tour nearby market towns. Nature reserves and heritage attractions are frequently suggested for day excursions.

  • Are there any pet friendly accommodations available in Chesterfield?

    Pet-friendly stays are available in Chesterfield, particularly around residential neighborhoods and near green spaces. Many hosts welcome pets and provide guidance on local dog walks.

  • What are some local tips for visiting Chesterfield?

    Arriving early for market days is frequently suggested, as you’ll find fresh produce and handmade goods. Carrying an umbrella is helpful, and locals often stroll Queen’s Park for relaxation.

  • What is Chesterfield known for?

    Chesterfield is known for its historic crooked church spire, vibrant outdoor markets, and access to the Peak District. The town blends local heritage with countryside appeal.

  • What are the best hidden gems to explore in Chesterfield?

    Wander lesser-known paths around the Chesterfield Canal, discover small galleries, or enjoy tucked-away cafés in Brampton. These spots provide quieter alternatives to main attractions.

  • What are the best foods to try in Chesterfield?

    Chesterfield has traditional pies, locally baked bread, and hearty pub fare. Afternoon tea is frequently suggested, with sweet treats and locally made cakes featured in cafés.

  • What should I bring for a trip to Chesterfield?

    Pack waterproof clothing and comfortable walking shoes, as rain can happen in any season. Layers are useful for changing temperatures, and a camera may help capture historic architecture and scenery.

  • What is the nightlife in Chesterfield like?

    Chesterfield has a mix of traditional pubs, relaxed bars, and venues with live music. The town center and Brampton area are known for welcoming atmospheres and community events.

  • What are the most popular events or festivals in Chesterfield?

    The Chesterfield Market Festival and annual medieval-themed events are often recommended. Seasonal celebrations, including local fairs and arts festivals, mark highlights on the town’s calendar.

  • Are there family friendly vacation rentals in Chesterfield?

    Many rentals in Chesterfield have family-friendly amenities and are located near parks, shopping, or leisure centers. Options often include homes or apartments with spacious layouts.